Cyclic disulfonate esters have been widely used, for example, as a therapeutic agent for leukemia.
Production of cyclic disulfonate esters had been conventionally carried out by a method in which an alkanedisulfonyl chloride is reacted with silver carbonate to form a corresponding silver alkanedisulfonate, and subsequently the resultant silver alkanedisulfonate is reacted with a dihaloalkane (Patent Document 1). However, this method had problems such as costly due to necessity to use silver carbonate; inefficient due to a long reaction time; and low yield of cyclic disulfonate ester to be obtained.
Therefore, as an improved method, another method had been developed in which an alkanedisulfonic anhydride, an alkanedisulfonic acid and/or a halogenated sulfonylalkanesulfonic acid is reacted with a diacyloxyalkane or a disulfonyloxyalkane (Patent Document 2).
However, this method was not necessarily satisfactory one because it had problems such as low isolated yield due to complicated procedures, although yield of cyclic disulfonate ester had been improved compared with that of the conventional method.
On the other hand, monosulfonate esters have been widely used for various functional materials (including polymers) such as, for example, alkylating agents, acid generating agents, medical products, agricultural chemicals, colorants, electrolyte materials, as well as intermediates for their syntheses.
As a method for producing monosulfonate ester, for example, a method had been known in which a sulfonic acid and a thionyl chloride are reacted to form a sulfonyl chloride, which is then reacted with a hydroxyl compound such as, for example, methanol in the presence of a basic catalyst such as, for example, pyridine, triethylamine, sodium hydroxide (Patent Document 3).
However, this method had such problems due to by-product of hydrochloric acid, for example, that when an unsaturated aliphatic sulfonic acid such as allyl sulfonic acid is esterified, a desired sulfonate ester cannot be obtained because the raw material is hydrochlorinated by hydrochloric acid generated as a by-product; and that production at an industrial scale is risky because hydrochloric acid is produced as a by-product in the reaction system; and the like.
Under such circumstances, development of a method for producing desired various types of sulfonate esters in high yield efficiently is demanded.    [Patent Document 1] JP-B-5-44946    [Patent Document 2] JP-A-2005-336155    [Patent Document 3] JP-A-11-246514